Title:
FLUORESCENT DYE, PREPARATION METHOD THEREFOR, AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2020/221217
Kind Code:
A1
Abstract:
A fluorescent dye, a preparation method therefor, and a use thereof; the fluorescent dye is sensitive and specific to viscosity response, has the advantage of low background fluorescence, and can be used as a fluorescence activated dot lighting probe for fluorescent labelling, quantification, or detection of proteins, enzymes, or nucleic acids.
Inventors:
ZHU LINYONG (CN)
YANG YI (CN)
ZHANG DASHENG (CN)
CHEN XIANJUN (CN)
LIN QIUNING (CN)
SU NI (CN)
YANG YI (CN)
ZHANG DASHENG (CN)
CHEN XIANJUN (CN)
LIN QIUNING (CN)
SU NI (CN)
Application Number:
PCT/CN2020/087311
Publication Date:
November 05, 2020
Filing Date:
April 27, 2020
Export Citation:
Assignee:
SHANGHAI GAOCHI ASSET MAN CO LTD (CN)
International Classes:
C07C255/58; C07C253/30; C07C255/53; C07D209/08; C07D213/85; C07D239/42; C07D241/20; C07D333/24; C07D333/36; C07D333/60; C07D409/14; C07D413/10; C07D455/04; C07D495/04; C07D495/14; C07F7/08; C09B23/10; C09B23/14; C09B57/00; C09K11/06; C12Q1/6851; G01N11/00; G01N21/64; G01N33/68
Domestic Patent References:
| WO2018014821A1 | 2018-01-25 | |||
| WO2014048547A1 | 2014-04-03 |
Foreign References:
| CN106939163A | 2017-07-11 | |||
| CN102399169A | 2012-04-04 | |||
| US5589506A | 1996-12-31 | |||
| JP2004262888A | 2004-09-24 | |||
| CN107663384A | 2018-02-06 | |||
| CN109574880A | 2019-04-05 | |||
| CN107641121A | 2018-01-30 | |||
| CN106349105A | 2017-01-25 |
Other References:
CHEN, XIANJUN ET AL.: "Visualizing RNA Dynamics in Live Cells with Bright and Stable Fluorescent RNAs", NATURE BIOTECHNOLOGY, vol. 37, no. 11, 23 September 2019 (2019-09-23), XP036920801, ISSN: 1546-1696, DOI: 20200621134430PX
LU, ZHUOQUN ET AL.: "Optical Waveguiding Organic Single Crystals Exhibiting Physical and Chemical Bending Features", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 59, no. 11, 29 January 2020 (2020-01-29), XP055751270, ISSN: 1521-3773, DOI: 20200621163621PX
LIM, CHANG-KEUN ET AL.: "Dye-Condensed Biopolymeric Hybrids: Chromophoric Aggregation and Self-Assembly toward Fluorescent Bionanoparticles for Near Infrared Bioimaging", CHEMISTRY OF MATERIALS, vol. 21, no. 24, 24 November 2009 (2009-11-24), XP055751274, ISSN: 1520-5002, DOI: 20200621134744X
OLIVER KAUMANNS ET AL.: "Nucleophilicities of the Anions of Arylacetonitriles and Arylpropionitriles in Dimethyl Sulfoxide", JOURNAL OF ORGANIC CHEMISTRY, vol. 74, no. 1, 26 November 2008 (2008-11-26), XP055049696, ISSN: 0022-3263, DOI: 20200621135440X
G. S'HEEREN ET AL.: "Synthesis of Frequency Doubling Nonlinear Optical Polymers, Functionalized with Aminocyano- and Alkoxycyano-Stilbene Dyes. Second Harmonic Generation in Corona Poled Thin Films", EUROPEAN POLYMER JOURNAL, vol. 30, no. 7, 31 July 1994 (1994-07-31), XP024052622, ISSN: 0014-3057, DOI: 20200621135645X
H.MUSTROPH : "UV/VIS Spectral Behavior of Azo Dyes. IX. The Absorption Behavior of Azo Dyes of 4’-Diethylamino-α-Cyanostilbene-4-Diazonium Ions", JOURNAL FUER SIGNALAUFZEICHNUNGS MATERIALIEN, vol. 12, no. 2, 31 December 1984 (1984-12-31), pages 115 - 120, XP009531154, ISSN: 0323-598X
T. VAN ES ET AL.: "Some Sulphonamido-Derivatives of Stilbene and Acetophenone", JOURNAL OF THE SOUTH AFRICAN CHEMICAL INSTITUTE, vol. 17, no. 2, 31 December 1964 (1964-12-31), XP055751278, ISSN: 0038-2078, DOI: 20200621140334X
P. PFEIFFER : "Theory of the Betaines. III = Zur Theorie der Betaine. III. Mitteilung. Experimentell bearbeitet von H. Behr, Br. Breyer, O. Clarenz und H. Kübler", JUSTUS LIEBIGS ANNALEN DER CHEMIE, vol. 465, 31 December 1928 (1928-12-31), pages 20 - 52, XP009531153, ISSN: 0075-4617, DOI: 10.1002/jlac.19284650104
DATABASE REGISTRY 29 April 2018 (2018-04-29), ANONYMOUS: "Benzeneacetonitrile, .alpha.-[(3-bromo-4-hydroxy-5- methoxyphenyl)methylene]-4-cyano- (CA INDEX NAME)", XP055858643, retrieved from STN Database accession no. 2221753-28-0
DATABASE REGISTRY 29 April 2018 (2018-04-29), ANONYMOUS: "Benzeneacetonitrile, 4-cyano-.alpha.-[(4-hydroxy-3- methoxyphenyl)methylene]- (CA INDEX NAME)", XP055858645, retrieved from STN Database accession no. 2221651-87-0
DATABASE REGISTRY 29 April 2018 (2018-04-29), ANONYMOUS: "Benzoic acid, 4-[2-(3-bromo-4-hydroxy-5-iodophenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858651, retrieved from STN Database accession no. 2221523-52-8
DATABASE REGISTRY 29 April 2018 (2018-04-29), ANONYMOUS: "Benzoic acid, 4-[2-(2-bromo-4-hydroxy-5-methoxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME) ", XP055858652, retrieved from STN Database accession no. 2221154-44-3
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[2-[3-bromo-4-(diethylamino)phenyl]-1-cyanoethenyl]- (CA INDEX NAME)", XP55858657, retrieved from STN Database accession no. 2221047-68-1
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(3-ethoxy-4-hydroxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858659, retrieved from STN Database accession no. 2220911-46-4
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(4-hydroxy-3-iodophenyl)ethenyl]- (CA INDEX NAME)", XP055858661, retrieved from STN Database accession no. 2220885-30-1
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(4-hydroxy-3-iodo-5-methoxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858663, retrieved from STN Database accession no. 2220883-25-8
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(2,3-dibromo-5-ethoxy-4-hydroxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858665, retrieved from STN Database accession no. 2220839-27-8
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[2-(3-chloro-4-hydroxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858666, retrieved from STN Database accession no. 2220838-14-0
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[2-(2-bromo-5-ethoxy-4-hydroxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858668, retrieved from STN Database accession no. 2220836-50-8
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(4-hydroxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858669, retrieved from STN Database accession no. 2220836-02-0
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[2-(3-bromo-4-hydroxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858671, retrieved from STN Database accession no. 2220834-27-3
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(4-hydroxy-3-methoxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858663, retrieved from STN Database accession no. 2220833-71-4
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(4-hydroxy-3-methoxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858677, retrieved from STN Database accession no. 2220685-06-1
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[2-(3-bromo-5-chloro-4-hydroxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858680, retrieved from STN Database accession no. 2220684-82-0
DATABASE REGISTRY 26 April 2018 (2018-04-26), ANONYMOUS: "Benzoic acid, 4-[2-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1- cyanoethenyl]- (CA INDEX NAME)", XP055858684, retrieved from STN Database accession no. 2219483-47-1
DATABASE REGISTRY 26 April 2018 (2018-04-26), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(3-ethoxy-4-hydroxy-5-iodophenyl)ethenyl]- (CA INDEX NAME)", XP055858685, retrieved from STN Database accession no. 2219482-61-6
DATABASE REGISTRY 26 April 2018 (2018-04-26), ANONYMOUS: " Benzoic acid, 4-[1-cyano-2-[4-hydroxy-3-methoxy-5-(2-propen-1- yl)phenyl]ethenyl]- (CA INDEX NAME)", XP055858687, retrieved from STN Database accession no. 2219463-03-1
DATABASE REGISTRY 26 April 2018 (2018-04-26), ANONYMOUS: "Benzoic acid, 4-[2-(3-chloro-5-ethoxy-4-hydroxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858692, retrieved from STN Database accession no. 2219461-41-1
DATABASE REGISTRY 26 April 2018 (2018-04-26), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(2,3-dibromo-4-hydroxy-5-methoxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858694, retrieved from STN Database accession no. 2219461-36-4
DATABASE REGISTRY 25 April 2018 (2018-04-25), ANONYMOUS, XP055858697, retrieved from STN Database accession no. 2219015-05-9
DATABASE REGISTRY 25 April 2018 (2018-04-25), ANONYMOUS: "Benzeneacetonitrile, .alpha.-[(3-bromo-4-hydroxyphenyl)methylene]-4-cyano- (CA INDEX NAME)", XP055858698, retrieved from STN Database accession no. 2218889-27-9
DATABASE REGISTRY 25 April 2018 (2018-04-25), ANONYMOUS: "Benzeneacetonitrile, 4-cyano-.alpha.-[(3-ethoxy-4-hydroxy-5- iodophenyl)methylene]- (CA INDEX NAME)", XP055858701, retrieved from STN Database accession no. 2218864-24-3
DATABASE REGISTRY 25 April 2018 (2018-04-25), ANONYMOUS: "Benzeneacetonitrile, .alpha.-[(3-bromo-5-ethoxy-4-hydroxyphenyl)methylene]- 4-cyano- (CA INDEX NAME)", XP055858706, retrieved from STN Database accession no. 2218860-32-1
DATABASE REGISTRY 24 April 2018 (2018-04-24), ANONYMOUS: "- Benzeneacetonitrile, 4-cyano-.alpha.-[(4-hydroxy-3,5- diiodophenyl)methylene]- (CA INDEX NAME)", XP055858707, retrieved from STN Database accession no. 2218151-87-0
DATABASE REGISTRY 24 April 2018 (2018-04-24), ANONYMOUS: "Benzeneacetonitrile, 4-cyano-.alpha.-[(3,5-dibromo-4- hydroxyphenyl)methylene]- (CA INDEX NAME)", XP055858708, retrieved from STN Database accession no. 2217743-67-2
DATABASE REGISTRY 24 April 2018 (2018-04-24), ANONYMOUS: " Benzeneacetonitrile, 4-cyano-.alpha.-[(4-hydroxy-3-iodo-5- methoxyphenyl)methylene]- (CA INDEX NAME)", XP055858713, retrieved from STN Database accession no. 2217738-28-6
DATABASE REGISTRY 5 June 2008 (2008-06-05), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858714, retrieved from STN Database accession no. 1025666-91-4
DATABASE REGISTRY 4 June 2008 (2008-06-04), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-[3-ethoxy-4-hydroxy-5-(2-propen-1- yl)phenyl]ethenyl]- (CA INDEX NAME)", XP055858715, retrieved from STN Database accession no. 1025322-92-2
DATABASE REGISTRY 4 June 2008 (2008-06-04), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-[4-(diethylamino)phenyl]ethenyl]- (CA INDEX NAME)", XP055858717, retrieved from STN Database accession no. 1025246-06-3
DATABASE REGISTRY 4 June 2008 (2008-06-04), ANONYMOUS: "Benzoic acid, 4-[2-(3-chloro-4-hydroxy-5-methoxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858720, retrieved from STN Database accession no. 1025227-78-4
DATABASE REGISTRY 3 June 2008 (2008-06-03), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858722, retrieved from STN Database accession no. 1025124-96-2
DATABASE REGISTRY 3 June 2008 (2008-06-03), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(3,5-dichloro-4-hydroxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858725, retrieved from STN Database accession no. 1024752-75-7
DATABASE REGISTRY 2 June 2008 (2008-06-02), ANONYMOUS: "Benzoic acid, 4-[2-(3-bromo-4-hydroxy-5-methoxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858729, retrieved from STN Database accession no. 1024709-74-7
DATABASE REGISTRY 2 June 2008 (2008-06-02), ANONYMOUS: "Benzoic acid, 4-[2-(3-bromo-5-ethoxy-4-hydroxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858733, retrieved from STN Database accession no. 1024672-75-0
DATABASE REGISTRY 24 January 2006 (2006-01-24), ANONYMOUS: "Benzoic acid, 4-[2-[3-bromo-4-(dimethylamino)phenyl]-1-cyanoethenyl]- (CA INDEX NAME)", XP055858736, retrieved from STN Database accession no. 872546-69-5
DATABASE REGISTRY 23 February 2005 (2005-02-23), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-[4-(diethylamino)-2-methoxyphenyl]ethenyl]- (CA INDEX NAME)", XP055858738, retrieved from STN Database accession no. 835894-06-9
DATABASE REGISTRY 17 February 2005 (2005-02-17), ANONYMOUS: "Benzeneacetonitrile, .alpha.-[(3-chloro-5-ethoxy-4- hydroxyphenyl)methylene]-4-cyano- (CA INDEX NAME)", XP055858741, retrieved from STN Database accession no. 832683-13-3
DATABASE REGISTRY 7 February 2005 (2005-02-07), ANONYMOUS: "Benzeneacetonitrile, 4-cyano-.alpha.-[(4-hydroxyphenyl)methylene]- (CA INDEX NAME)", XP055858743, retrieved from STN Database accession no. 827011-74-5
DATABASE REGISTRY 3 February 2005 (2005-02-03), ANONYMOUS: "Benzeneacetonitrile, .alpha.-[(3-chloro-4-hydroxy-5- methoxyphenyl)methylene]-4-cyano- (CA INDEX NAME)", XP055858747, retrieved from STN Database accession no. 824974-06-3
DATABASE REGISTRY 20 July 2004 (2004-07-20), ANONYMOUS: "Benzeneacetonitrile, .alpha.-[[3-bromo-4-(dimethylamino)phenyl]methylene]- 4-cyano- (CA INDEX NAME)", XP055858750, retrieved from STN Database accession no. 713104-90-6
DATABASE REGISTRY 10 August 2001 (2001-08-10), ANONYMOUS: "3,5-Pyridinedicarbonitrile, 2,4-diamino-6-[1-cyano-2-[4-[methyl(3- methylbutyl)amino]phenyl]ethenyl]- (CA INDEX NAME)", XP055858751, retrieved from STN Database accession no. 351065-38-8
DATABASE REGISTRY 4 March 2014 (2014-03-04), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-(4-hydroxyphenyl)ethenyl]-, 1-methylethyl ester (CA INDEX NAME)", XP055858755, retrieved from STN Database accession no. 1562283-43-5
DATABASE REGISTRY 4 March 2014 (2014-03-04), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-[4-(dimethylamino)phenyl]ethenyl]-, 1-methylethyl ester (CA INDEX NAME)", XP055858758, retrieved from STN Database accession no. 1562311-50-5
DATABASE REGISTRY 4 March 2014 (2014-03-04), ANONYMOUS, retrieved from STN Database accession no. 156223-81-2
DATABASE REGISTRY 4 March 2014 (2014-03-04), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-(2,4-dihydroxyphenyl)ethenyl]-, 1-methylethyl ester (CA INDEX NAME)", XP055858763, retrieved from STN Database accession no. 1562326-45-7
DATABASE REGISTRY 6 March 2014 (2014-03-06), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-, methyl ester (CA INDEX NAME)", XP055858775, retrieved from STN Database accession no. 1563251-01-3
DATABASE REGISTRY 6 March 2014 (2014-03-06), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-(4-hydroxyphenyl)ethenyl]-, methyl ester (CA INDEX NAME)", XP055858778, retrieved from STN Database accession no. 1563281-43-5
DATABASE REGISTRY 6 March 2014 (2014-03-06), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-[4-(diethylamino)phenyl]ethenyl]-, methyl ester (CA INDEX NAME)", XP055858783, retrieved from STN Database accession no. 1563300-10-6
DATABASE REGISTRY 6 March 2014 (2014-03-06), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-[4-(dimethylamino)phenyl]ethenyl]-, methyl ester (CA INDEX NAME)", XP055858789, retrieved from STN Database accession no. 1563438-71-0
DATABASE REGISTRY 6 March 2014 (2014-03-06), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-(2,4-dihydroxyphenyl)ethenyl]-, methyl ester (CA INDEX NAME)", XP055858791, retrieved from STN Database accession no. 1563471-00-0
DATABASE REGISTRY 6 March 2014 (2014-03-06), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-, 1-methylethyl ester (CA INDEX NAME)", XP055858798, retrieved from STN Database accession no. 1563491-13-3
JOHANNES GIERSCHNER ET AL.: "Preparation and Optical Properties of Oligophenylenevinylene/perhydrotriphenylene Inclusion Compounds", ADVANCED MATERIALS, vol. 12, no. 10, 29 February 2000 (2000-02-29), XP000958777, ISSN: 0935-9648, DOI: 20200621165151X
I. G. BINEV ET AL.: "Nitrile Frequency and Intensity-Structure Relationships of Trans-1, 2-Diaryl-Acrylonitriles/ L.F.E.R. and Quantum-Chemical Approaches", IZVESTIYA PO KHIMIYA, vol. 12, no. 2, 31 December 1979 (1979-12-31), XP009122581, ISSN: 0324-0401, DOI: 20200621171346X
I. G. BINEV ET AL.: "Infrared Spectra and Structure of Carbanions. XII. Dimeric Dianions Derived from α, β-Diarylacrylonitriles", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 141, no. 2, 31 December 1977 (1977-12-31), XP055751285, ISSN: 0022-328X, DOI: 20200621171641X
D. CHERNEVA: "Kinetics and Mechanism of the Reaction of Ozone with Substituted Cyanostilbenes in the Liquid Phase. I", IZVESTIYA PO KHIMIYA, vol. 10, no. 1, 31 December 1977 (1977-12-31), pages 84 - 87, XP009531159, ISSN: 0324-0401
I.G. BINEV : "Infrared Spectra and Structure of Carbanions. V. Carbanions-Intermediates in Nucleophilic Addition Reactions to α, β-Diarylcyanoethylenes", IZVESTIYA PO KHIMIYA, vol. 9, no. 1, 31 December 1976 (1976-12-31), pages 33 - 51, XP009531158, ISSN: 0324-0401
E.FEYTMANS-DE MEDICIS : "Constantes d'acidité, à l'état excité, des a-cyanostilbènes et des a-cyanodiphénylazomethines paradiméthylamines - [Acidity Constants in the Excited State of p-Dimethylamino=α-Cyanostilbenes and α-Cyanodiphenylazomethines] ", BULLETIN DE LA CLASSE DES SCIENCES, ACADEMIE ROYALE DE BELGIQUE, vol. 53, no. 11, 31 December 1967 (1967-12-31), pages 1259 - 1265, XP009531157, ISSN: 0001-4141
E.FEYTMANS-DE MEDICIS ET AL.: "Spectrographic Detection Method for Active Methylenes and the Synthesis of Some Styrene, Cyanostilbene, and Cyanazomethine Derivatives. X. Kinetics of Stilbene and Azomethine Condensations", BULLETIN DES SOCIETES CHIMIQUES BELGES, vol. 75, no. 11-12, 31 December 1966 (1966-12-31), XP009531156, ISSN: 0037-9646
E.FEYTMANS-DE MEDICIS: "Acid-Base Equilibria of 4'-Dimethylamino-α-Cyanostilbene and Derivatives. II. m- and p-Cyano Compounds = Équilibre acide-base du diméthylamino-4',alpha-cyanostilbène et de ses dérivés de substitution. II. Dérives méta et para-cyanes", BULLETIN DES SOCIETES CHIMIQUES BELGES, vol. 72, 31 December 1963 (1963-12-31), pages 642 - 643, XP009531155, ISSN: 0037-9646
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See also references of EP 3964496A4
LU, ZHUOQUN ET AL.: "Optical Waveguiding Organic Single Crystals Exhibiting Physical and Chemical Bending Features", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 59, no. 11, 29 January 2020 (2020-01-29), XP055751270, ISSN: 1521-3773, DOI: 20200621163621PX
LIM, CHANG-KEUN ET AL.: "Dye-Condensed Biopolymeric Hybrids: Chromophoric Aggregation and Self-Assembly toward Fluorescent Bionanoparticles for Near Infrared Bioimaging", CHEMISTRY OF MATERIALS, vol. 21, no. 24, 24 November 2009 (2009-11-24), XP055751274, ISSN: 1520-5002, DOI: 20200621134744X
OLIVER KAUMANNS ET AL.: "Nucleophilicities of the Anions of Arylacetonitriles and Arylpropionitriles in Dimethyl Sulfoxide", JOURNAL OF ORGANIC CHEMISTRY, vol. 74, no. 1, 26 November 2008 (2008-11-26), XP055049696, ISSN: 0022-3263, DOI: 20200621135440X
G. S'HEEREN ET AL.: "Synthesis of Frequency Doubling Nonlinear Optical Polymers, Functionalized with Aminocyano- and Alkoxycyano-Stilbene Dyes. Second Harmonic Generation in Corona Poled Thin Films", EUROPEAN POLYMER JOURNAL, vol. 30, no. 7, 31 July 1994 (1994-07-31), XP024052622, ISSN: 0014-3057, DOI: 20200621135645X
H.MUSTROPH : "UV/VIS Spectral Behavior of Azo Dyes. IX. The Absorption Behavior of Azo Dyes of 4’-Diethylamino-α-Cyanostilbene-4-Diazonium Ions", JOURNAL FUER SIGNALAUFZEICHNUNGS MATERIALIEN, vol. 12, no. 2, 31 December 1984 (1984-12-31), pages 115 - 120, XP009531154, ISSN: 0323-598X
T. VAN ES ET AL.: "Some Sulphonamido-Derivatives of Stilbene and Acetophenone", JOURNAL OF THE SOUTH AFRICAN CHEMICAL INSTITUTE, vol. 17, no. 2, 31 December 1964 (1964-12-31), XP055751278, ISSN: 0038-2078, DOI: 20200621140334X
P. PFEIFFER : "Theory of the Betaines. III = Zur Theorie der Betaine. III. Mitteilung. Experimentell bearbeitet von H. Behr, Br. Breyer, O. Clarenz und H. Kübler", JUSTUS LIEBIGS ANNALEN DER CHEMIE, vol. 465, 31 December 1928 (1928-12-31), pages 20 - 52, XP009531153, ISSN: 0075-4617, DOI: 10.1002/jlac.19284650104
DATABASE REGISTRY 29 April 2018 (2018-04-29), ANONYMOUS: "Benzeneacetonitrile, .alpha.-[(3-bromo-4-hydroxy-5- methoxyphenyl)methylene]-4-cyano- (CA INDEX NAME)", XP055858643, retrieved from STN Database accession no. 2221753-28-0
DATABASE REGISTRY 29 April 2018 (2018-04-29), ANONYMOUS: "Benzeneacetonitrile, 4-cyano-.alpha.-[(4-hydroxy-3- methoxyphenyl)methylene]- (CA INDEX NAME)", XP055858645, retrieved from STN Database accession no. 2221651-87-0
DATABASE REGISTRY 29 April 2018 (2018-04-29), ANONYMOUS: "Benzoic acid, 4-[2-(3-bromo-4-hydroxy-5-iodophenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858651, retrieved from STN Database accession no. 2221523-52-8
DATABASE REGISTRY 29 April 2018 (2018-04-29), ANONYMOUS: "Benzoic acid, 4-[2-(2-bromo-4-hydroxy-5-methoxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME) ", XP055858652, retrieved from STN Database accession no. 2221154-44-3
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[2-[3-bromo-4-(diethylamino)phenyl]-1-cyanoethenyl]- (CA INDEX NAME)", XP55858657, retrieved from STN Database accession no. 2221047-68-1
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(3-ethoxy-4-hydroxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858659, retrieved from STN Database accession no. 2220911-46-4
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(4-hydroxy-3-iodophenyl)ethenyl]- (CA INDEX NAME)", XP055858661, retrieved from STN Database accession no. 2220885-30-1
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(4-hydroxy-3-iodo-5-methoxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858663, retrieved from STN Database accession no. 2220883-25-8
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(2,3-dibromo-5-ethoxy-4-hydroxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858665, retrieved from STN Database accession no. 2220839-27-8
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[2-(3-chloro-4-hydroxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858666, retrieved from STN Database accession no. 2220838-14-0
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[2-(2-bromo-5-ethoxy-4-hydroxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858668, retrieved from STN Database accession no. 2220836-50-8
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(4-hydroxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858669, retrieved from STN Database accession no. 2220836-02-0
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[2-(3-bromo-4-hydroxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858671, retrieved from STN Database accession no. 2220834-27-3
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(4-hydroxy-3-methoxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858663, retrieved from STN Database accession no. 2220833-71-4
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(4-hydroxy-3-methoxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858677, retrieved from STN Database accession no. 2220685-06-1
DATABASE REGISTRY 27 April 2018 (2018-04-27), ANONYMOUS: "Benzoic acid, 4-[2-(3-bromo-5-chloro-4-hydroxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858680, retrieved from STN Database accession no. 2220684-82-0
DATABASE REGISTRY 26 April 2018 (2018-04-26), ANONYMOUS: "Benzoic acid, 4-[2-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1- cyanoethenyl]- (CA INDEX NAME)", XP055858684, retrieved from STN Database accession no. 2219483-47-1
DATABASE REGISTRY 26 April 2018 (2018-04-26), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(3-ethoxy-4-hydroxy-5-iodophenyl)ethenyl]- (CA INDEX NAME)", XP055858685, retrieved from STN Database accession no. 2219482-61-6
DATABASE REGISTRY 26 April 2018 (2018-04-26), ANONYMOUS: " Benzoic acid, 4-[1-cyano-2-[4-hydroxy-3-methoxy-5-(2-propen-1- yl)phenyl]ethenyl]- (CA INDEX NAME)", XP055858687, retrieved from STN Database accession no. 2219463-03-1
DATABASE REGISTRY 26 April 2018 (2018-04-26), ANONYMOUS: "Benzoic acid, 4-[2-(3-chloro-5-ethoxy-4-hydroxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858692, retrieved from STN Database accession no. 2219461-41-1
DATABASE REGISTRY 26 April 2018 (2018-04-26), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(2,3-dibromo-4-hydroxy-5-methoxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858694, retrieved from STN Database accession no. 2219461-36-4
DATABASE REGISTRY 25 April 2018 (2018-04-25), ANONYMOUS, XP055858697, retrieved from STN Database accession no. 2219015-05-9
DATABASE REGISTRY 25 April 2018 (2018-04-25), ANONYMOUS: "Benzeneacetonitrile, .alpha.-[(3-bromo-4-hydroxyphenyl)methylene]-4-cyano- (CA INDEX NAME)", XP055858698, retrieved from STN Database accession no. 2218889-27-9
DATABASE REGISTRY 25 April 2018 (2018-04-25), ANONYMOUS: "Benzeneacetonitrile, 4-cyano-.alpha.-[(3-ethoxy-4-hydroxy-5- iodophenyl)methylene]- (CA INDEX NAME)", XP055858701, retrieved from STN Database accession no. 2218864-24-3
DATABASE REGISTRY 25 April 2018 (2018-04-25), ANONYMOUS: "Benzeneacetonitrile, .alpha.-[(3-bromo-5-ethoxy-4-hydroxyphenyl)methylene]- 4-cyano- (CA INDEX NAME)", XP055858706, retrieved from STN Database accession no. 2218860-32-1
DATABASE REGISTRY 24 April 2018 (2018-04-24), ANONYMOUS: "- Benzeneacetonitrile, 4-cyano-.alpha.-[(4-hydroxy-3,5- diiodophenyl)methylene]- (CA INDEX NAME)", XP055858707, retrieved from STN Database accession no. 2218151-87-0
DATABASE REGISTRY 24 April 2018 (2018-04-24), ANONYMOUS: "Benzeneacetonitrile, 4-cyano-.alpha.-[(3,5-dibromo-4- hydroxyphenyl)methylene]- (CA INDEX NAME)", XP055858708, retrieved from STN Database accession no. 2217743-67-2
DATABASE REGISTRY 24 April 2018 (2018-04-24), ANONYMOUS: " Benzeneacetonitrile, 4-cyano-.alpha.-[(4-hydroxy-3-iodo-5- methoxyphenyl)methylene]- (CA INDEX NAME)", XP055858713, retrieved from STN Database accession no. 2217738-28-6
DATABASE REGISTRY 5 June 2008 (2008-06-05), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858714, retrieved from STN Database accession no. 1025666-91-4
DATABASE REGISTRY 4 June 2008 (2008-06-04), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-[3-ethoxy-4-hydroxy-5-(2-propen-1- yl)phenyl]ethenyl]- (CA INDEX NAME)", XP055858715, retrieved from STN Database accession no. 1025322-92-2
DATABASE REGISTRY 4 June 2008 (2008-06-04), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-[4-(diethylamino)phenyl]ethenyl]- (CA INDEX NAME)", XP055858717, retrieved from STN Database accession no. 1025246-06-3
DATABASE REGISTRY 4 June 2008 (2008-06-04), ANONYMOUS: "Benzoic acid, 4-[2-(3-chloro-4-hydroxy-5-methoxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858720, retrieved from STN Database accession no. 1025227-78-4
DATABASE REGISTRY 3 June 2008 (2008-06-03), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858722, retrieved from STN Database accession no. 1025124-96-2
DATABASE REGISTRY 3 June 2008 (2008-06-03), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-(3,5-dichloro-4-hydroxyphenyl)ethenyl]- (CA INDEX NAME)", XP055858725, retrieved from STN Database accession no. 1024752-75-7
DATABASE REGISTRY 2 June 2008 (2008-06-02), ANONYMOUS: "Benzoic acid, 4-[2-(3-bromo-4-hydroxy-5-methoxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858729, retrieved from STN Database accession no. 1024709-74-7
DATABASE REGISTRY 2 June 2008 (2008-06-02), ANONYMOUS: "Benzoic acid, 4-[2-(3-bromo-5-ethoxy-4-hydroxyphenyl)-1-cyanoethenyl]- (CA INDEX NAME)", XP055858733, retrieved from STN Database accession no. 1024672-75-0
DATABASE REGISTRY 24 January 2006 (2006-01-24), ANONYMOUS: "Benzoic acid, 4-[2-[3-bromo-4-(dimethylamino)phenyl]-1-cyanoethenyl]- (CA INDEX NAME)", XP055858736, retrieved from STN Database accession no. 872546-69-5
DATABASE REGISTRY 23 February 2005 (2005-02-23), ANONYMOUS: "Benzoic acid, 4-[1-cyano-2-[4-(diethylamino)-2-methoxyphenyl]ethenyl]- (CA INDEX NAME)", XP055858738, retrieved from STN Database accession no. 835894-06-9
DATABASE REGISTRY 17 February 2005 (2005-02-17), ANONYMOUS: "Benzeneacetonitrile, .alpha.-[(3-chloro-5-ethoxy-4- hydroxyphenyl)methylene]-4-cyano- (CA INDEX NAME)", XP055858741, retrieved from STN Database accession no. 832683-13-3
DATABASE REGISTRY 7 February 2005 (2005-02-07), ANONYMOUS: "Benzeneacetonitrile, 4-cyano-.alpha.-[(4-hydroxyphenyl)methylene]- (CA INDEX NAME)", XP055858743, retrieved from STN Database accession no. 827011-74-5
DATABASE REGISTRY 3 February 2005 (2005-02-03), ANONYMOUS: "Benzeneacetonitrile, .alpha.-[(3-chloro-4-hydroxy-5- methoxyphenyl)methylene]-4-cyano- (CA INDEX NAME)", XP055858747, retrieved from STN Database accession no. 824974-06-3
DATABASE REGISTRY 20 July 2004 (2004-07-20), ANONYMOUS: "Benzeneacetonitrile, .alpha.-[[3-bromo-4-(dimethylamino)phenyl]methylene]- 4-cyano- (CA INDEX NAME)", XP055858750, retrieved from STN Database accession no. 713104-90-6
DATABASE REGISTRY 10 August 2001 (2001-08-10), ANONYMOUS: "3,5-Pyridinedicarbonitrile, 2,4-diamino-6-[1-cyano-2-[4-[methyl(3- methylbutyl)amino]phenyl]ethenyl]- (CA INDEX NAME)", XP055858751, retrieved from STN Database accession no. 351065-38-8
DATABASE REGISTRY 4 March 2014 (2014-03-04), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-(4-hydroxyphenyl)ethenyl]-, 1-methylethyl ester (CA INDEX NAME)", XP055858755, retrieved from STN Database accession no. 1562283-43-5
DATABASE REGISTRY 4 March 2014 (2014-03-04), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-[4-(dimethylamino)phenyl]ethenyl]-, 1-methylethyl ester (CA INDEX NAME)", XP055858758, retrieved from STN Database accession no. 1562311-50-5
DATABASE REGISTRY 4 March 2014 (2014-03-04), ANONYMOUS, retrieved from STN Database accession no. 156223-81-2
DATABASE REGISTRY 4 March 2014 (2014-03-04), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-(2,4-dihydroxyphenyl)ethenyl]-, 1-methylethyl ester (CA INDEX NAME)", XP055858763, retrieved from STN Database accession no. 1562326-45-7
DATABASE REGISTRY 6 March 2014 (2014-03-06), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-, methyl ester (CA INDEX NAME)", XP055858775, retrieved from STN Database accession no. 1563251-01-3
DATABASE REGISTRY 6 March 2014 (2014-03-06), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-(4-hydroxyphenyl)ethenyl]-, methyl ester (CA INDEX NAME)", XP055858778, retrieved from STN Database accession no. 1563281-43-5
DATABASE REGISTRY 6 March 2014 (2014-03-06), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-[4-(diethylamino)phenyl]ethenyl]-, methyl ester (CA INDEX NAME)", XP055858783, retrieved from STN Database accession no. 1563300-10-6
DATABASE REGISTRY 6 March 2014 (2014-03-06), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-[4-(dimethylamino)phenyl]ethenyl]-, methyl ester (CA INDEX NAME)", XP055858789, retrieved from STN Database accession no. 1563438-71-0
DATABASE REGISTRY 6 March 2014 (2014-03-06), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-(2,4-dihydroxyphenyl)ethenyl]-, methyl ester (CA INDEX NAME)", XP055858791, retrieved from STN Database accession no. 1563471-00-0
DATABASE REGISTRY 6 March 2014 (2014-03-06), ANONYMOUS: "2-Furancarboxylic acid, 5-[1-cyano-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-, 1-methylethyl ester (CA INDEX NAME)", XP055858798, retrieved from STN Database accession no. 1563491-13-3
JOHANNES GIERSCHNER ET AL.: "Preparation and Optical Properties of Oligophenylenevinylene/perhydrotriphenylene Inclusion Compounds", ADVANCED MATERIALS, vol. 12, no. 10, 29 February 2000 (2000-02-29), XP000958777, ISSN: 0935-9648, DOI: 20200621165151X
I. G. BINEV ET AL.: "Nitrile Frequency and Intensity-Structure Relationships of Trans-1, 2-Diaryl-Acrylonitriles/ L.F.E.R. and Quantum-Chemical Approaches", IZVESTIYA PO KHIMIYA, vol. 12, no. 2, 31 December 1979 (1979-12-31), XP009122581, ISSN: 0324-0401, DOI: 20200621171346X
I. G. BINEV ET AL.: "Infrared Spectra and Structure of Carbanions. XII. Dimeric Dianions Derived from α, β-Diarylacrylonitriles", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 141, no. 2, 31 December 1977 (1977-12-31), XP055751285, ISSN: 0022-328X, DOI: 20200621171641X
D. CHERNEVA: "Kinetics and Mechanism of the Reaction of Ozone with Substituted Cyanostilbenes in the Liquid Phase. I", IZVESTIYA PO KHIMIYA, vol. 10, no. 1, 31 December 1977 (1977-12-31), pages 84 - 87, XP009531159, ISSN: 0324-0401
I.G. BINEV : "Infrared Spectra and Structure of Carbanions. V. Carbanions-Intermediates in Nucleophilic Addition Reactions to α, β-Diarylcyanoethylenes", IZVESTIYA PO KHIMIYA, vol. 9, no. 1, 31 December 1976 (1976-12-31), pages 33 - 51, XP009531158, ISSN: 0324-0401
E.FEYTMANS-DE MEDICIS : "Constantes d'acidité, à l'état excité, des a-cyanostilbènes et des a-cyanodiphénylazomethines paradiméthylamines - [Acidity Constants in the Excited State of p-Dimethylamino=α-Cyanostilbenes and α-Cyanodiphenylazomethines] ", BULLETIN DE LA CLASSE DES SCIENCES, ACADEMIE ROYALE DE BELGIQUE, vol. 53, no. 11, 31 December 1967 (1967-12-31), pages 1259 - 1265, XP009531157, ISSN: 0001-4141
E.FEYTMANS-DE MEDICIS ET AL.: "Spectrographic Detection Method for Active Methylenes and the Synthesis of Some Styrene, Cyanostilbene, and Cyanazomethine Derivatives. X. Kinetics of Stilbene and Azomethine Condensations", BULLETIN DES SOCIETES CHIMIQUES BELGES, vol. 75, no. 11-12, 31 December 1966 (1966-12-31), XP009531156, ISSN: 0037-9646
E.FEYTMANS-DE MEDICIS: "Acid-Base Equilibria of 4'-Dimethylamino-α-Cyanostilbene and Derivatives. II. m- and p-Cyano Compounds = Équilibre acide-base du diméthylamino-4',alpha-cyanostilbène et de ses dérivés de substitution. II. Dérives méta et para-cyanes", BULLETIN DES SOCIETES CHIMIQUES BELGES, vol. 72, 31 December 1963 (1963-12-31), pages 642 - 643, XP009531155, ISSN: 0037-9646
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See also references of EP 3964496A4
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